5-t-butyloxycarbonylamino-2-hydroxybenzonitrile | 554409-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-t-butyloxycarbonylamino-2-hydroxybenzonitrile
• 英文别名: tert-Butyl (3-cyano-4-hydroxyphenyl)carbamate；tert-butyl N-(3-cyano-4-hydroxyphenyl)carbamate
• CAS: 554409-15-3
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: HKAUAHVWKXYUDM-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-t-butyloxycarbonylamino-2-hydroxybenzonitrile 在 lithium aluminium tetrahydride 、 TEA 、 potassium acetate 、 氯磷酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4'R,2''R,4''R)-2'-(5-t-btyloxycarbonylamino-2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid
  参考文献：
  名称：

  Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues

  摘要：

  The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3"N-Boc-pyochelin, 3"-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00010-6
• 作为产物：
  描述：

  2-羟基-5-硝基苯甲腈 在 sodium carbonate 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 5-t-butyloxycarbonylamino-2-hydroxybenzonitrile
  参考文献：
  名称：

  Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues

  摘要：

  The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3"N-Boc-pyochelin, 3"-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00010-6

文献信息

• Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa
  作者：Sabrina Noël、Françoise Hoegy、Freddy Rivault、Didier Rognan、Isabelle J. Schalk、Gaëtan L.A. Mislin

  DOI：10.1016/j.bmcl.2013.11.054

  日期：2014.1

  Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties (Fe-55 uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa. (C) 2013 Elsevier Ltd. All rights reserved.
• Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues
  作者：A Zamri、I.J Schalk、F Pattus、M.A Abdallah

  DOI：10.1016/s0960-894x(03)00010-6

  日期：2003.3

  The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3"N-Boc-pyochelin, 3"-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. (C) 2003 Elsevier Science Ltd. All rights reserved.